Makeup is fun!
I think, you oughtn't be afraid to play around with it, no one is going to say... "you didn't follow the rules!" Although pricey tools may make it easier, you don't need them. Qtips and fingers work fine!
I do line my top eyelid with eyeliner (black even, but I have a dark complexion). I have a hard time doing it with my eyes open, so I poke the outer corner of my lid to make sure it stays shut.
Work from the inner eye to the outer. I have little advice about the lower lid (I'm squeamish when it comes to eyes). Some people do above the lower eyelashes, some on.
To blend eyeshadow, I use a brush. Sometimes, I use my finger. Qtips work too. Most of the time, I use my finger.
For lipstick, I don't use a liner to keep it from bleeding. I remember as a young teen, friends spent hours on their makeup. You don't really have to. Don't be afraid to be colorful. I once saw on a TV program that bright reds make your smile look whiter and the ladies on there said to not be afraid to just sweep it across your lips- it doesn't have to be perfect. So I've followed their advice!
When I'm feeling particularly fancy,
I shade in my eyebrows too. Just lightly, to give them more definition.
The more you put makeup on, the easier it gets. I've been wearing makeup for such a long time, that I can get some of the stuff on without looking in the mirror.
Here's a picture of my face, made-up in just a couple of minutes (blush, eyeliner, eyeshadow, lipstick):
It isn't perfect (looks like I missed part of my lid, huh?
), but it's fun and I think people don't really even notice if something's a bit off... everyone's preoccupied with how their own face looks.
ETA: A before makeup photo of me. These are rare, so this one is like a year old!